When Will Roland isn’t in rehearsal for Broadway’s highly anticipated Dear Evan Hansen, he’s working his other day job.

Though Roland makes his Broadway debut in Evan Hansen’s virtual playground of Facebook groups, emails, tweets, and viral videos, his world offstage is much more concrete. His family owns downtown auction house Roland Auctions, which is deep into selling a mass collection of political ephemera. And as Roland examines the artifacts, he can’t help but draw parallels between the 2016 election and campaigns of America’s past—parallels that comfort him.

“Dealing with all these objects definitely helps me sleep a little better,” he says. “It just feels like, ‘Here we are, it’s the same old argument.’ In 1888, Benjamin Harrison ran, and then again in 1916 Woodrow Wilson ran on the exact same platform that Donald Trump is running on, which is protect American industries, limit immigration, Benjamin Harrison said, ‘No half-paid competition with foreign labor.’ And Wilson was a little more subtle about it; he just printed a lot of buttons that said ‘America first.’ It was the same sort of xenophobic, isolationist, high tariff, and trade deals that protected American labor above all else. There’s definitely an element of ‘It’s the same thing over and over again.’ It’s a little calming.”

In anticipation of tomorrow’s election—and a whole new slew of political ephemera that, no doubt, someone has already started collecting—Roland takes us through a bit of history and the idea that, much as in Dear Evan Hansen, we learn from what we leave behind.

Dr. Alan York

“Alan York, he was an optometrist living in East Hampton who was friends with a lot of artists like Jackson Pollock and Willem de Kooning—they were all his clients out in East Hampton. He started collecting in the ’30s, so by the mid-’50s he was already a really established collector. He continued to collect through the ’90s.”

George Washington Inaugural Button

“That inaugural button is a great bit of New York history. Down at Federal/Liberty Hall, he was inaugurated right on the steps there. All these manufacturers in the city were selling souvenir buttons from his inauguration. There are different variations on them, some say ‘Long Live the President,’ some have the 13 colonies on them.”

Jefferson Davis Pin

“This is a really fascinating one. It was manufactured in February or March of 1861. Jefferson Davis was the president of the Confederacy and P.G.T. Beauregard was his top general, and these were made to sort of promote their popularity throughout the Confederate States of America. These pins were also manufactured for presidential elections in 1860 and 1864, and they were double-sided. Men would have a ribbon and pin it to their lapel—a sort of proto button, the earliest version of wearing your candidate’s face on your jacket.”

Kennedy and Johnson Pin

“This is a very, very rare Kennedy and Johnson button. There were millions and millions of Kennedy buttons manufactured, but only a few thousand of that variation specifically, either because it was for a specific event or it was for a specific region.”

Wendell Willkie Campgain Buttons

”Wilkie ran in ’40 against FDR. So it was the third election in a row where the Republicans were really trying to ruin FDR. When you look at button collecting, there are more Wilkie buttons than anything else because they spent millions and millions of dollars. The have all these crazy slogans calling [FDR] a dictator and saying, “We don’t want Eleanor either.” It got very nasty. In response to years and years of the GOP manufacturing all these buttons, the Democrats put out this button saying, “All you get from Wilkie are buttons,” which I thought was really fun. I was looking at some of these FDR slogans and thinking, “Hillary should use these.” There’s one that says, “Wilkie for the millionaires, FDR for the millions.” That’s a great anti-one-percenter slogan right there.

FDR was elected president of the United States four times in a row, ’44, ’40, ’36, and ’32. We did not have that [two-term presidency] rule. That was instated after FDR. Roosevelt ran the whole election totally in a wheelchair. No one knew. It was this amazing secret. He had his own underground platform at Grand Central where they could take him out of the train, he could get into his car all without being seen by the public. It was this elaborate cover-up that the president was sick and in a wheelchair, all to save face during the wartime, and then he ended up dying in office, and Truman became president.“

Eugene Debbs and Benjamin Hanford Pin

“Eugene Debs is the most successful third party candidate to have ever made a bid for the presidency. He (and Theodore Roosevelt in 1912) remains on the very short list of third party candidates to have won ten percent of the popular vote or more, and Debs was as socialist candidate and Hanford was his running mate. Debs ran in 1900, 1904, 1908—he ran like five times—and in 1920 when he ran, he actually conducted his candidacy from a prison cell in Georgia. He was a political prisoner for dissent during World War I; Woodrow Wilson had thrown him in jail. They had all these buttons that were like “Elect convict number ‘29643’!” It was literally his mug shot on the button.”

William Henry Harrison Campaign Pin

“Before 1840, which was the year that William Henry Harrison ran for president, campaigns did not manufacture campaign items. It was less of a national dialogue. Harrison was the first to mass produce hundreds of thousands of items promoting his bid for the presidency. He used this log cabin image in almost all of his stuff and the idea was “I’m just a regular guy, I grew up in a log cabin, I’m just like you, I’m a man of the people.” Again, you want to talk about narratives recurring and recurring and recurring.”

Abraham Lincoln and Andrew Johnson Brass Pin

“[This pin] is Lincoln and his running mate, Andrew Johnson. Johnson became the president when Lincoln got shot. Lincoln and Stephen Douglass, his opponent, had these crazy debates down at the Cooper Union in NYC. Lincoln stayed in the St. Dennis hotel, which was at the time a fancy uptown hotel and is the building that our auction house is housed in. That’s one of my favorite bits of connection. That is one of only six or seven of this variety to exist in the world. It’s made of brass, and the two portraits are what you would call ferrotypes or tintypes, which was an early photo process which would expose right on to metal or tin and then they would put it under a layer of glass and set it into the pin. It’s exceptionally rare to find those in good shape—or at all, for that matter.”

Franklin D. Roosevelt Senate Campaign Pin

“We were talking about FDR being elected president four times, but his first office that he ever ran for was in 1912: He ran for New York state senate and he lost. That was the only election that he ever lost and that button was the first item FDR manufactured to promote any campaign.”

Dr. York and His Collectibles

“In the late 19th century, they had this campaign tactic called torch bearing, where people would go out in the street and ‘bear a torch for Benjamin Harrison.’ I don’t know if they would holler about their candidate or if they would argue for him at bars and stuff, but every candidacy had these torch bearers as a part of it.”

President Harry S. Truman holding the Chicago Daily Tribune and Will Roland Holding That Very Paper

“That’s Harry Truman! Dewey lost, but the Chicago Daily Tribune called it wrong and sent it to press too early and then sent out like a million papers that said ‘Dewey Defeats Truman,’ and Truman took that great photo the next day with the paper.”